Screening of microbial esterases for asymmetric hydrolysis of 2-ethylhexyl butyrate
A pH indicator agar plate method was used to screen for esterase activities for hydrolysis of 2-ethylhexyl butyrate. Seven hundred and fifty-seven selected microbial cultures, including 325 bacteria, and 432 yeasts and actinomycetes from the ARS Culture, Collection, were screened. Among them, 62 cultures hydrolyzed 2-ethylhexyl butyrate. Of these strains only 17 showed lipase activity on a rhodamine B lipase screen. The reaction products, 2-ethyl-1-hexanol andn-butyric acid were confirmed by gas-liquid chromatography (GC) and GC/MS analyses. The yield of 2-ethyl-1-hexanol varied depending on the strains of the microorganisms, with the highest yield at 79.1% by a strain ofPseudomonas myxogenes Product analyses with a cyclodextrin GC chiral column showed that two strains ofPseudomonas produced, greater than 80% enantiomeric excess of S(+)-2-ethyl-1-hexanol.
Key wordsEsterase Ethylhexyl butyrate Hydrolytic stereospecificity
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- 1.Barton, M.J., J.P. Hamman, K.C. Fichter and G.J. Calton. 1990. Enzymic resolution of R,S-2-(4-hydroxyphenoxy)propionic acid. Enzyme Microbiol. Technol. 12: 577–583.Google Scholar
- 2.Hauck, R.S., C. Wegner, P. Blumtritt, J.H. Fuhrhop and H. Nau. 1990. Asymmetric synthesis and teratogenic acitivity of(R)- and (S)-2-ethylhexanoic acid, a metabolite of the plasticizer di-(2-ethylhexyl)phthalate. Life Sci. 46: 513–518.Google Scholar
- 3.Hou, C.T. and T.M. Johnston. 1992. Screening of lipase activities with cultures from the Agricultural Research Service Culture Collection. J. Am. Oil Chem. Soc. 69, No. 11, in press.Google Scholar
- 4.Iriuchijema, S. and A. Keiyu. 1981. Asymmetric hydrolysis of (+/-)-alpha-substituted carboxylic acid esters with micro-organisms. Agric. Biol. Chem. 45: 1389–1392.Google Scholar
- 5.Iwai, M., S. Okumura and Y. Tsujisaka. 1980. Synthesis of terpene alcohol esters by lipase. Agric. Biol. Chem. 44: 2731–2732.Google Scholar
- 6.Okumura, S., M. Iwai and Y. Tsujisaka. 1979. Synthesis of various kinds of esters by four microbial lipases. Biochim. Biophys. Acta. 575: 156–165.Google Scholar
- 7.Sih, C.J., Q.-M. Gu, G. Fulling, S.-H. Wu and D.R. Reddy. 1988. The use of microbial enzymes for the synthesis of optically active pharmaceuticals. Dev. Ind. Microbiol. 29: 221–229Google Scholar
- 8.Tsujisaka, Y. and M. Iwai. 1984. Comparative study on microbial lipases. Kagaku to Kogyo 58: 60–69.Google Scholar
- 9.Yamamoto, Y., K. Yamamoto, T. Nishioka and J. Oda. 1988. Asymmetric synthesis of optically active lactones from cyclic acid anhydrides using lipase in organic solvents. Agric. Biol. Chem. 52: 3087–3092.Google Scholar